EP0118327A1 - Kationische Latices aus konjugierten Dienen - Google Patents

Kationische Latices aus konjugierten Dienen Download PDF

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Publication number
EP0118327A1
EP0118327A1 EP84400120A EP84400120A EP0118327A1 EP 0118327 A1 EP0118327 A1 EP 0118327A1 EP 84400120 A EP84400120 A EP 84400120A EP 84400120 A EP84400120 A EP 84400120A EP 0118327 A1 EP0118327 A1 EP 0118327A1
Authority
EP
European Patent Office
Prior art keywords
cationic
unsaturated
nitrogen compound
weight
tertiary nitrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP84400120A
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English (en)
French (fr)
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EP0118327B1 (de
Inventor
Frédéric Leising
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhodia Chimie SAS
Original Assignee
Rhone Poulenc Specialites Chimiques
Rhone Poulenc Chimie SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Specialites Chimiques, Rhone Poulenc Chimie SA filed Critical Rhone Poulenc Specialites Chimiques
Priority to AT84400120T priority Critical patent/ATE26722T1/de
Publication of EP0118327A1 publication Critical patent/EP0118327A1/de
Application granted granted Critical
Publication of EP0118327B1 publication Critical patent/EP0118327B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F295/00—Macromolecular compounds obtained by polymerisation using successively different catalyst types without deactivating the intermediate polymer

Definitions

  • the present invention relates to cationic latexes based on conjugated dienes obtained by emulsion polymerization.
  • the latices thus obtained cannot be used in basic medium because their density of cationic charges at basic pH is very low.
  • the aim of the Applicant has been to prepare cationic latexes which can be used whatever the pH.
  • non-hydrolyzable tertiary unsaturated nitrogen compound in an acid or alkaline medium means any unsaturated nitrogen compound free of quaternary ammonium group, having a nitrogen atom trisubstituted by hydrocarbon groups and a hydrolysis rate not exceeding 5 % in acidic or alkaline medium at the polymerization temperature.
  • said non-hydrolyzable unsaturated tertiary nitrogen compound can be brought into contact with the reaction medium (A) at any stage of the polymerization operation of the nonionogenic monomer (s) copolymerizable with the non-hydrolyzable tertiary nitrogen compound .
  • reaction medium (A) can be completely present in the reaction medium (A) from the start of the first polymerization step, in particular when the latter is not carried out to its end; it can also be introduced continuously or discontinuously throughout the 1st polymerization stage, in particular if the latter is complete; Similarly, it can only be introduced into the reaction medium (A) after a certain degree of transformation of the nonionic monomer (s) (from 30% for example) or else at the end of the first polymerization step (by example between 90 and 98% of the transformation rate).
  • Said nonionogenic monomers can be used alone or else as a mixture with one another when they are copolymerizable with one another.
  • the substances generating cationic charges which can be used are non-hydrolysable or partially hydrolysable products, that is to say products whose hydrolysis rate under the polymerization reaction conditions is less than or equal to approximately 50%.
  • unsaturated polycoordinated onium salts of an element from groups VB and VIB means any salt having an onium cation in which all the valences of the element from groups VB and VIB are satisfied by hydrocarbon groups, an element the free valence is saturated with a carbon atom, at least one of said hydrocarbon groups being unsaturated.
  • Products corresponding to this formula are trimethylaminoethylacrylamide chloride, trimethylaminopropylacrylamide or methacrylamide bromide, trimethylaminobutylacrylamide or methacrylamide methyl sulfate, trimethylaminopropylmethacrylate chloride.
  • the use of the cationic charge-generating substance in the reaction medium (A) may be prior to that of the non-hydrolyzable tertiary unsaturated nitrogen compound or concomitant with that of said unsaturated nitrogen compound.
  • Said substance generating cationic charges can also be present in the reaction medium (A) at the start of the polymerization operation by means of a "cationic seed", that is to say a polymer or copolymer previously prepared by aqueous emulsion polymerization in a cationic medium of the non-ionogenic monomer (s) in the presence of the desired quantity of substance generating cationic charges.
  • a cationic seed that is to say a polymer or copolymer previously prepared by aqueous emulsion polymerization in a cationic medium of the non-ionogenic monomer (s) in the presence of the desired quantity of substance generating cationic charges.
  • the copolymerization operation of the unsaturated nitrogen compound and of the ionogenic monomer (s) constituting the 1st stage of the process. making it possible to prepare the cationic latexes which are the subject of the invention is carried out under the conventional polymer conditions rization in aqueous emulsion in a cationic medium at a temperature between 60 and 90 ° C and generally between 75 and 85 ° C, at any pH (which can vary from 3 to 12 and preferably from 5 to 9) in the presence of a cationic or non-ionic initiator, optionally of a cationic or non-ionic emulsifying agent and in addition in the presence of the substance generating cationic charges, said substance consisting of an unsaturated copolymerizable salt of polycoordinated onium of an element of the group VB or VIB and / or an excess of cationic initiator.
  • the cationic initiators which can be used are those already mentioned above as an example of a substance which generates cationic charges.
  • the quantity of initiator used to carry out the polymerization operation depends on the monomer (s) used and on the polymerization temperature; this is generally of the order of 0.1 to 5% by weight relative to the total weight of monomers, and preferably of the order of 0.1 to 2%.
  • the initiator or the emulsifier is the main constituent or one of the constituents of the substance generating the cationic charges, an excess in proportion to these quantities must be used.
  • the amount of cationic or non-ionic emulsifier used to stabilize the copolymer particles can range up to 2% of the total weight of monomers.
  • conjugated dienes which can be used to carry out the second step of the process making it possible to prepare the cationic latexes which are the subject of the invention, mention may be made of butadiene, isoprene, chloroprene, 1,3-pentadiene , dimethylbutadiene, cyclopentadiene ....
  • the quantity of nonionogenic monomer (s) possibly present next to the conjugated diene to carry out the 2nd stage can reach approximately 80% by weight of the total quantity of nonionogenic monomer (s) used to produce the whole. of the process.
  • the second copolymerization step can be carried out under temperature and pH conditions similar to those of the 1st step, optionally in the presence of a chain-limiting agent and an additional quantity of uncharged initiator or cationic radical generator if necessary.
  • chain limiters mention may be made of: mercaptans such as n-butyl-, n-octyl-, n-lauryl-, t-dodecyl-mercaptan; halogenated derivatives such as: carbon tetrabromide ...
  • the cationic latexes of copolymers based on conjugated dienes which are the subject of the invention have a zeta potential which can vary from +80 mV to +20 mV when the pH varies from 2 to 12 for example.
  • Said cationic latexes can be used as binders for coating paper, for preparing non-woven webs, for coating metallic substrates, etc.
  • the reaction is stopped by cooling after 11 hours of total operation.
  • the conversion rate is 99%.
  • the cationic nature of the dispersion thus prepared is demonstrated by measuring the zeta potential as a function of the pH.
  • the measurement is carried out using a MARK II microelectrophoresis device manufactured by RANK BROTHERS and carried out at a concentration of 0.05% of polymer under a measurement voltage of 80 volts and at a temperature of 25 ° C.
  • the autoclave is brought to a temperature of 75 ° C.
  • the reaction is stopped by cooling after 12 h 30 min of running.
  • the reaction is stopped by cooling after 12 h 30 min of running.
  • the product obtained is a dispersion having the following characteristics:
  • the zeta potential measurement results are as follows:
  • Example 2 The operations described in Example 2 are repeated, however replacing the methyl methacrylate in the 2nd step with the same weight of butyl acrylate.
  • Example 2 The operations described in Example 2 are repeated, however replacing the methyl methacrylate in the 2nd step with the same weight of acrylonitrile.
  • the autoclave is brought to a temperature of 75 °. 15 g of 2,2 'azobis (2-amidinopropane) hydrochloride are introduced.
  • the reaction is stopped by cooling after a total running time of 12 h 30 min.
  • Example 5 The operations described in Example 5 are repeated, however limiting the conversion rate at the end of the 1st stage to 50% instead of 90% (approximately 10 minutes of reaction).
  • Cold loading is carried out in an autoclave with a capacity of 5 liters and fitted with a propeller-type agitator rotating at 150 rpm:
  • the reaction is stopped by cooling after 11 hours of The reaction is stopped by cooling after 11 hours of total running.
  • the conversion rate is 99%.
  • Example 1 The operation described in the 1st step of Example 1 is repeated, replacing the 15 g of trimethylaminopropylmethacrylamide chloride with 15 g of 1-methyl-2 vinylpyridinium chloride.
  • the reaction is then allowed to proceed for 4 hours at 75 ° C; the transformation rate is then 90%.
  • the reaction is stopped by cooling after 9 hours of total operation.
  • An aqueous dispersion is obtained having the following characteristics.
  • Example 5 The operation described in the 1st step of Example 5 is repeated, replacing the 159 g of styrene with 159 g of butyl acrylate (i.e. 288 g of butyl acrylate in total).
  • step 2 of example 5 The operation described in step 2 of example 5 is repeated.
  • step 1 of Example 5 The operation described in step 1 of Example 5 is repeated, replacing the 129 g of butyl acrylate with 129 g of styrene (ie 288 g of styrene in total).
  • step 2 of example 5 The operation described in step 2 of example 5 is repeated.
  • step 1 of example 5 The operation described in step 1 of example 5 is repeated. limiting the conversion rate to 30% instead of 90%.
  • step 2 of example 5 The operation described in step 2 of example 5 is repeated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Paper (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP84400120A 1983-01-28 1984-01-20 Kationische Latices aus konjugierten Dienen Expired EP0118327B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT84400120T ATE26722T1 (de) 1983-01-28 1984-01-20 Kationische latices aus konjugierten dienen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8301303 1983-01-28
FR8301303A FR2540127B1 (de) 1983-01-28 1983-01-28

Publications (2)

Publication Number Publication Date
EP0118327A1 true EP0118327A1 (de) 1984-09-12
EP0118327B1 EP0118327B1 (de) 1987-04-22

Family

ID=9285369

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84400120A Expired EP0118327B1 (de) 1983-01-28 1984-01-20 Kationische Latices aus konjugierten Dienen

Country Status (15)

Country Link
US (1) US4791161A (de)
EP (1) EP0118327B1 (de)
JP (1) JPS59142217A (de)
AT (1) ATE26722T1 (de)
BR (1) BR8400343A (de)
CA (1) CA1224584A (de)
DE (1) DE3463273D1 (de)
DK (1) DK37984A (de)
ES (1) ES8500290A1 (de)
FI (1) FI76815C (de)
FR (1) FR2540127B1 (de)
IE (1) IE56628B1 (de)
NO (1) NO162290C (de)
PT (1) PT78024B (de)
YU (1) YU43664B (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003048441A1 (en) * 2001-11-30 2003-06-12 National Starch And Chemical Investment Holding Corporation Crosslinkable cationic emulsion binders and their use as a binder for nonwovens
WO2007063317A1 (en) * 2005-12-01 2007-06-07 Halliburton Energy Services, Inc. Wellbore sealant compositions containing cationic latexes and methods of using them
US7687440B2 (en) 2005-12-01 2010-03-30 Halliburton Energy Services, Inc. Wellbore sealant compositions containing cationic latexes
US7694738B2 (en) 2005-12-01 2010-04-13 Halliburton Energy Services, Inc. Methods of using wellbore sealant compositions containing cationic latexes

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JPH0751692B2 (ja) * 1985-07-05 1995-06-05 アクゾ・ナ−ムロ−ゼ・フエンノ−トシヤツプ 導電性基体の塗装方法およびカチオン性バインダ−をベ−スとする水性塗料
US5045576A (en) * 1988-08-04 1991-09-03 The Dow Chemical Company Latex conversion to cationic form use, for example in cationic asphalt emulsion
US5250602A (en) * 1990-01-31 1993-10-05 Mitsui-Cyanamid, Ltd. Polymer emulsion and method for preparing the same
US5260354A (en) * 1992-03-06 1993-11-09 Ppg Industries, Inc. Additives for electrodepositable coating compositions
US5709714A (en) * 1996-03-11 1998-01-20 Rohm And Haas Company Method of treating leather with amphoteric polymers
US6184287B1 (en) * 1999-01-26 2001-02-06 Omnova Solutions Inc. Polymeric latexes prepared in the presence of 2-acrylamido-2-methylpropanesulfonate
US7279452B2 (en) 2000-06-12 2007-10-09 Commun-I-Tec, Ltd. Sanitizing applicator having a positively charged fabric cover
US6667290B2 (en) 2001-09-19 2003-12-23 Jeffrey S. Svendsen Substrate treated with a binder comprising positive or neutral ions
UA81258C2 (en) 2002-08-09 2007-12-25 Akzo Nobel Coatings Int Bv Quaternized polymer with acidic blocking groups, method for obtaining and use thereof, and composition, containing this polymer
US20070015873A1 (en) * 2005-07-13 2007-01-18 Fenn David R Electrodepositable aqueous resinous dispersions and methods for their preparation
US7576042B2 (en) * 2006-02-28 2009-08-18 Halliburton Energy Services, Inc. Salt water stable latex cement slurries
US9598588B2 (en) 2012-05-16 2017-03-21 Ppg Industries Ohio, Inc. Cationic electrodepositable coating compositions capable of forming low gloss coatings
US9505937B2 (en) 2012-05-16 2016-11-29 Ppg Industries Ohio, Inc. Anionic electrodepositable coating compositions capable of forming low gloss coatings
US20140162910A1 (en) 2012-12-10 2014-06-12 Halliburton Energy Services, Inc. Wellbore Servicing Compositions and Methods of Making and Using Same
US10066146B2 (en) 2013-06-21 2018-09-04 Halliburton Energy Services, Inc. Wellbore servicing compositions and methods of making and using same

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US3399159A (en) * 1967-02-06 1968-08-27 Kendall & Co Cationic latices and method of preparing same
GB2013221A (en) * 1978-01-27 1979-08-08 Kao Corp Fabric sizing emulsion
US4337185A (en) * 1980-06-23 1982-06-29 The Dow Chemical Company Process for making cationic structured particle latexes using reactive polymeric surfactants

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US2808388A (en) * 1955-07-29 1957-10-01 Eastman Kodak Co Hydrosols of acrylic esters and hydrophobic monomers polymerized with cationic or ampholytic hydrophilic copolymers and process for making same
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GB2013221A (en) * 1978-01-27 1979-08-08 Kao Corp Fabric sizing emulsion
US4337185A (en) * 1980-06-23 1982-06-29 The Dow Chemical Company Process for making cationic structured particle latexes using reactive polymeric surfactants

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003048441A1 (en) * 2001-11-30 2003-06-12 National Starch And Chemical Investment Holding Corporation Crosslinkable cationic emulsion binders and their use as a binder for nonwovens
WO2007063317A1 (en) * 2005-12-01 2007-06-07 Halliburton Energy Services, Inc. Wellbore sealant compositions containing cationic latexes and methods of using them
US7687440B2 (en) 2005-12-01 2010-03-30 Halliburton Energy Services, Inc. Wellbore sealant compositions containing cationic latexes
US7694738B2 (en) 2005-12-01 2010-04-13 Halliburton Energy Services, Inc. Methods of using wellbore sealant compositions containing cationic latexes

Also Published As

Publication number Publication date
BR8400343A (pt) 1984-09-04
PT78024A (fr) 1984-02-01
IE840195L (en) 1984-07-28
FR2540127A1 (de) 1984-08-03
FI840339A0 (fi) 1984-01-27
ES529221A0 (es) 1984-10-01
FI840339A (fi) 1984-07-29
DK37984D0 (da) 1984-01-27
EP0118327B1 (de) 1987-04-22
US4791161A (en) 1988-12-13
NO162290C (no) 1989-12-06
FR2540127B1 (de) 1985-03-29
CA1224584A (fr) 1987-07-21
YU13084A (en) 1986-06-30
DE3463273D1 (en) 1987-05-27
NO162290B (no) 1989-08-28
ATE26722T1 (de) 1987-05-15
DK37984A (da) 1984-07-29
YU43664B (en) 1989-10-31
JPS59142217A (ja) 1984-08-15
FI76815B (fi) 1988-08-31
ES8500290A1 (es) 1984-10-01
NO840305L (no) 1984-07-30
JPS625930B2 (de) 1987-02-07
IE56628B1 (en) 1991-10-23
FI76815C (fi) 1988-12-12
PT78024B (fr) 1986-03-27

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